Free resource · For founders
Startup Lawyer Interview Scorecard
Six questions for the first call, and how to score the answers.
Jason Acevedo | Updated October 13, 2026
Most founders hire a lawyer the way they would hire a plumber: someone recommended one, the first call went fine, done. The first call is where you learn almost everything you need to know, if you ask the right six questions and listen for the shape of the answer rather than the confidence of it. Score each lawyer from 1 to 5 on each question, tick any red flags you saw, and compare. The lawyer with the highest score is not automatically the right one, but a low score on question 1 or 3 almost always is the wrong one.
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Lawyer 1: 0 / 30 · 0 red flags
Lawyer 2: 0 / 30 · 0 red flags
Lawyer 3: 0 / 30 · 0 red flags
The six questions
| # | Question | Lawyer 1 | Lawyer 2 | Lawyer 3 |
|---|---|---|---|---|
| 1 | How many venture financings did you close in the past year? What you want to hear: A number and a couple of stories. Anyone doing this work steadily can describe recent deals without naming clients. What you do not: An assurance instead of a number, or a change of subject. | |||
| 2 | Who will do the day-to-day work? What you want to hear: A named person you get to meet, with their own closed deals to point at. Partner-sells, associate-does can work well when the team is experienced. What you do not: Vagueness about staffing, or a partner you will never see again after this call. | |||
| 3 | How do you scope and price? What you want to hear: A walk-through of what the work involves and a realistic estimate with assumptions attached. What you do not: A suspiciously round number with no scope behind it. That is a guess dressed up as a number. | |||
| 4 | What happens when a term sheet lands Friday afternoon? What you want to hear: A real story about pace on a recent deal. Fundraising does not keep business hours. What you do not: A policy statement about turnaround times. | |||
| 5 | Do you know my industry? What you want to hear: Describe what you are building in two sentences and ask what they would want to see first. Speed and specificity tell you whether they have done it before. What you do not: A generic answer that would fit any company. | |||
| 6 | Who will you introduce me to, and what realistically happens after that? What you want to hear: A narrow, specific answer about what their last few introductions actually produced. Narrow is usually the honest one. What you do not: Investor relationships framed as a path to a check. |
Red flags, all checkable in one meeting
Tick any you saw. One is a question to ask again; two or more is an answer.
| Red flag | Lawyer 1 | Lawyer 2 | Lawyer 3 |
|---|---|---|---|
| A generalist who "does startups too" but goes quiet when asked for the last three financings | |||
| A fee quote with no assumptions behind it | |||
| A partner you meet once at the pitch and never again | |||
| No founder references offered (anyone good has clients happy to take your call) | |||
| Reluctance to talk about cost up front | |||
| Investor relationships pitched as a way to get you funded |
Reading the score
Twenty-four or better with no red flags is someone you can hire. Between eighteen and twenty-four, look at where the points were lost: a low score on deal volume (question 1) or pricing (question 3) is hard to work around, while a low score on introductions (question 6) is often just an honest lawyer. Below eighteen, or any lawyer with two red flags, keep looking. And weight question 2 by how you answered it: the day-to-day person is the one you are actually hiring.
Where to go next
The questions come from How Do I Find a Good Startup Lawyer in Philadelphia?, which also covers where the good referrals come from and the three firm models. How Much Does a Startup Lawyer Cost? gives you the market ranges to test question 3 against. If you are earlier than hiring counsel, the Seed-Stage Legal Checklist tells you what you will be asking them to do.
This scorecard is general information, not legal advice, and using it does not create an attorney-client relationship. If you want to run the six questions on me, get in touch.